GB459594A - Improvements in dyeing artificial shaped objects - Google Patents

Improvements in dyeing artificial shaped objects

Info

Publication number
GB459594A
GB459594A GB10849/35A GB1084935A GB459594A GB 459594 A GB459594 A GB 459594A GB 10849/35 A GB10849/35 A GB 10849/35A GB 1084935 A GB1084935 A GB 1084935A GB 459594 A GB459594 A GB 459594A
Authority
GB
United Kingdom
Prior art keywords
product
heating
dyed
acid
mol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB10849/35A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ACETA GmbH
Original Assignee
ACETA GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ACETA GmbH filed Critical ACETA GmbH
Priority to GB10849/35A priority Critical patent/GB459594A/en
Priority to FR800339D priority patent/FR800339A/en
Priority to US58259A priority patent/US2127236A/en
Publication of GB459594A publication Critical patent/GB459594A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/443Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00Dyes not provided for by a single group of this subclass
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00Dyes not provided for by a single group of this subclass
    • C09B69/001Dyes containing an onium group attached to the dye skeleton via a bridge
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/40Cellulose acetate
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/30Polarising elements
    • G02B5/3025Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Coloring (AREA)

Abstract

Artificial shaped bodies, such as fibres, filaments, ribbons, bristles, sheets or films of plastic materials soluble in organic solvents and capable of forming films and belonging to the cellulose derivative or artificial resin types which bodies contain components having at least 10 to 12 carbon atoms in the molecule and carrying salt-forming acid groups, such components being substantially incapable of being washed-out with water (cf. Specification 459,711), are dyed with a basic dyestuff capable of forming water-soluble salts with acids and containing one or more strongly basic groups not in themselves essential to the presence of the colour. Alternatively, the material is treated with a corresponding dyestuff derivative or intermediate product, e.g. an azo coupling component, containing the strongly basic group or groups and the dyestuff is formed therefrom upon the material, e.g. by treatment, locally if desired, with a diazo component. The dyestuffs may be of the azo, di- or tri-phenylmethane, xanthene, acridine, azine, oxazine, triazine, aminonaphthalimide or indigoid classes, amino- or aminooxyanthraquinones, anthraquinonyl mercaptans or sulphides, anthraquinolines or anthrapyrimidines and may contain metal in complex union introduced before, during or after the dyeing; alternatively the materials may be preliminarily treated with a solution of the agent yielding the metal, in which case the dyestuffs of British Specification 305,648, [Class 2 (iii)], or German Specification 582,689 may suitably be applied. Preferably the dyestuffs have the strongly basic groups not directly connected to a chromogen residue. The suitable dyestuffs are of the following general formul (in which Ar represents a chromogen residue, R represents hydrogen, alkyl or substituted alkyl, R<1> represents alkyl or substituted alkyl, Alk represents alkylene, An represents a monovalent anion and <FORM:0459594/IV/1> represents pentavalent basic nitrogen, which may be linked to three residues R<1> or may form part of a pyridine ring) viz.- <FORM:0459594/IV/2> ; <FORM:0459594/IV/3> , e.g. the product obtainable by heating the azo dye, p-nitraniline --> 1 - (b -aminoethyl)aminonaphthalene, with methylisothiourea sulphate; <FORM:0459594/IV/4> e.g. the product obtainable by heating with dimethyl sulphate the azo dye obtainable by coupling with b -naphthol the diazo compound of the amine obtained by heating with dilute hydrochloric acid the thiourea from methyl isothiocyanate and the product of heating sodium p-formylaminophenolate with chlorethylamine in alcohol; <FORM:0459594/IV/5> e.g. the azo dyestuff 4-b -diethylaminoethyl-b -oxyethylaniline --> dimethylaniline; <FORM:0459594/IV/6> e.g. the product obtainable by reacting chloracetyl chloride with the azo dyestuff 4-b -oxyethylaniline --> b -naphthol and heating the product with piperidine in alcohol; <FORM:0459594/IV/7> e.g. the product obtainable as in the first step of (5) with replacement of the chloracetyl chloride by cyanamide hydrochloride; <FORM:0459594/IV/8> e.g. the product of reaction of 1 : 4-di-(g -chloro-b - oxypropylamino)anthraquinone with b - aminoethylmercaptan; <FORM:0459594/IV/9> e.g. the product of reaction of 1 : 4-di-(g -chloro-b -oxypropylamino)anthraquinone with ethylenethiourea in methylglycol; <FORM:0459594/IV/100> e.g. the product of reaction of dimethyl sulphate on the thioether from sodium methylmercaptan and 1 : 4-di-(g -chloro-b -oxypropylamino)anthraquinone; <FORM:0459594/IV/111> <FORM:0459594/IV/122> <FORM:0459594/IV/133> <FORM:0459594/IV/144> <FORM:0459594/IV/155> <FORM:0459594/IV/166> e.g. the product obtained by heating with methyl iodide in methylglycol under pressure the azo dyestuff obtainable by coupling with phenol the diazo compound of the amine obtained by reducing the nitro group of the product of reaction of m-nitraniline with methylisocyanate; <FORM:0459594/IV/17> e.g. the product obtained by heating with piperidine the azo dyestuff obtainable by coupling with b -naphthol the diazo compound of the amine obtained by hydrolysis of monobrominated p-acetylaminoacetophenone; <FORM:0459594/IV/18> e.g. the azo dyestuff, cresidine --> salicylic acid diethylaminoethyl ester; <FORM:0459594/IV/19> e.g. the product obtainable by heating 1-aminoanthraquinone-2-carboxylic acid methyl ester with excess of b -diethylaminoethylamine at 120 DEG C.; <FORM:0459594/IV/20> e.g. the product of reaction of 1-aminoanthraquinone-2-sulphochloride with b -diethylaminoethylamine in chloroform; <FORM:0459594/IV/21> e.g. azo dyestuffs from diazotized m-aminophenyltrimethylammonium or p-aminophenylpyridinium chloride or 1-aminoanthraquinonyl pyridinium compounds; <FORM:0459594/IV/22> Advantageously, the dyestuffs contain additional residues which increase the affinity for the material to be dyed and the following such residues are specified, viz. OH, <FORM:0459594/IV/23> , NO2 Alk--OH, O--Alk--OH, COOR<1>, Alk--COOR<1>, <FORM:0459594/IV/24> Various general methods of preparation of the dyestuffs are specified. The basic groups may be eliminated by hydrolysis after the dyeing or printing operation, e.g. after dyeing with the pyridinium compound from a chloracetylated p-oxyazo dye or from the 4-chloromethylbenzenesulphonic acid ester of leucothioindigo or with dyestuffs containing basic groups obtained by the action of basic substituted isocyanates or of ester chlorides of aminoalcohols, e.g. chloroformic acid-b -diethylaminoethyl ester. Level dyeing may be facilitated by the use of assistants having active cations, e.g. dodecylanine acetate, dodecyltrimethylammonium chloride or oleylaminoethylmethyldiethylammonium methosulphate or of swelling agents or hydrotropic agents, e.g. sodium tetrahydronaphthalenesulphonate. The dyeings may be fixed by after-treatment with an oxycarboxylic or oxysulphonic acid, tannin, an aluminium or other metal salt or an amine or quaternary ammonium compound of high molecular weight or may be overdyed with acid dyestuffs such as Quinoline yellow S or Alizarine direct blue A. The following examples are specified: (1) acetate artificial silk containing 10 per cent of the polymerisation product from maleic anhydride (1 mol.) and vinyl chloride (1 mol.) is dyed by treatment for 1 hour in a bath at 75 DEG C., feebly acid with acetic acid, containing the dyestuff obtained by heating 1 : 4-di-(p-oxyphenylamino) anthraquinone (1 mol.) with b -chlorethyldiethylamine hydrochloride (2 mols.) and sodium (2 mols.) in glycol monoethyl ether at 130 DEG C.; (2) acetate artificial silk containing 10 per cent of the polymerisation product from maleic anhydride (1 mol.) and vinyl chloracetate (4 mols.) is suspended for 8 hours in moist air at 80 DEG C. containing trimethylamine and is then dyed as in (1) in a bath containing sodium acetate and acetic acid with the condensation obtained by heating 1 : 4-di-(g -chloro - b - oxypropylamino) anthraquinone with an excess of morpholine in presence of fused potassium acetate and copper powder; (3) acetate artificial silk containing 10 per cent of the polymerisation product from maleic anhydride (1 mol.) and vinyl ethyl ether (1 mol.) is similarly dyed with Janus brown B; (4) the artificial silk of (1) is similarly dyed with 2 - methoxy - 6 - chloro - 9 - a - diethylamino - g -pentylaminoacridine or its monomethiodide and top dyed with Alizarine direct blue A; (5) the artificial silk of (1) is similarly dyed with 1 : 8 - diaminoanthraquinone - 4 - pyridinium chloride; (6) the artificial silk of (1) is similarly dyed with the dyestuff obtainable by reacting 5 - bromindol - 2 : 2<1> - thionaphthene indigo with pyridine in presence of aluminium chloride; (7) the artificial silk of (1) is similarly dyed with Tannin orange R; the artificial silk of (1) is similarly dyed with the condensation product obtained by heating 1-amino-4-chloranthraquinone with excess of g -dimethylamino-n-propylamine in presence of fused potassium acetate and copper acetate; (9) acetate artificial silk containing 12,5 per cent of a mixed ester containing 2,1 acetyl groups and 0,7 maleic acid residue per glucose unit is similarly dyed with the product obtained by heating the azo dyestuff from diazotized Fast red GL base and 2 - oxy - 3 - chloracetylaminonaphthalene with pyridine at 100 DEG C.; (10) acetate artificial silk containing 10 per cent of the ester acid obtained by heating with methanol the polymerisation product from maleic anhydride (1 mol.) and vinyl chloride (1 mol.) is dyed in a bath at 30 DEG C. containing acetic acid, diazotized fast GL base and the pyridinium salt from chloracetyl-2-naphthol and the dyeing is developed with a solution of sodium acetate or dilute ammonia; (11) acetate artificial silk containing 8 per cent of the polymerisation product from maleic anhydride (1 mol.) and vinyl methyl glycol ether is dyed in a bath at 30--70 DEG C. containing the product obtainable by the action of pyridine on the product of chloracetylation of the azo dyestuff, p-nitraniline --> 1-naphthol and the dyeing is fixed by treatment with a weakly ammoniacal solution of octodecyltrimethylammonium bromide. 4 - b - Diethylaminoethyl - b - oxyethylaniline is obtained by heating 4-aminophenylethyl alcohol hydrochloride (1 mol.) with benzoyl chloride (2 mols.) in benzene, saponifying the resulting dibenzoyl derivative with alcoholic soda to remove one benzoyl group, dissolving the product in a solution of sodium methylate (1 mol.), evaporating to dryness, heating the resulting alcoholate with b -diethylaminoethyl chloride in benzene and boiling with hydrochloric acid to remove the remaining benzoyl group. Chloroformic acid-b -diethylaminoethyl ester is obtained as hydrochloride by the action of phosgene on a solution of b -diethylaminoethyl alcohol in chloroform. g -Dimethylamino-n-propylamine is obtained by catalytic reduction of b -dimethylaminopropionitrile. 2 - Oxy
GB10849/35A 1935-01-11 1935-04-08 Improvements in dyeing artificial shaped objects Expired GB459594A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB10849/35A GB459594A (en) 1935-01-11 1935-04-08 Improvements in dyeing artificial shaped objects
FR800339D FR800339A (en) 1935-01-11 1936-01-02 Process of dyeing formed artificial products
US58259A US2127236A (en) 1935-01-11 1936-01-09 Dyeing artificial shaped articles

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE800339X 1935-01-11
DE2127236X 1935-01-11
GB10849/35A GB459594A (en) 1935-01-11 1935-04-08 Improvements in dyeing artificial shaped objects

Publications (1)

Publication Number Publication Date
GB459594A true GB459594A (en) 1937-01-08

Family

ID=61562912

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10849/35A Expired GB459594A (en) 1935-01-11 1935-04-08 Improvements in dyeing artificial shaped objects

Country Status (3)

Country Link
US (1) US2127236A (en)
FR (1) FR800339A (en)
GB (1) GB459594A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3084990A (en) * 1958-08-08 1963-04-09 Du Pont Shaped articles of modified cellulose esters
US3278486A (en) * 1959-02-17 1966-10-11 Scripto Inc Colored polymeric materials
US3619105A (en) * 1967-09-22 1971-11-09 Eastman Kodak Co Cellulose ester fiber with d,hexyl sodium sulfosuccinate therein and dyeing thereof
US3857675A (en) * 1970-11-16 1974-12-31 H Schwab Mixtures of two chromogenic compounds
DE3433545A1 (en) * 1984-09-13 1986-03-20 Bayer Ag, 5090 Leverkusen BASIC DIOXAZINE DYES

Also Published As

Publication number Publication date
FR800339A (en) 1936-07-02
US2127236A (en) 1938-08-16

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